3666-82-8Relevant academic research and scientific papers
Reductive Knoevenagel Condensation with the Zn-AcOH System
Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 1285 - 1291 (2020/11/13)
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Design, Synthesis, and Structure-Activity Relationship Study of Pyrazolones as Potent Inhibitors of Pancreatic Lipase
Zhang, Jing,Yang, Yang,Qian, Xing-Kai,Song, Pei-Fang,Zhao, Yi-Shu,Guan, Xiao-Qing,Zou, Li-Wei,Bao, Xiaoze,Wang, Hong
supporting information, p. 1600 - 1604 (2021/03/03)
Pancreatic lipase (PL), a key target for the prevention and treatment of obesity, plays crucial roles in the hydrolysis and absorption of in dietary fat. In this study, a series of pyrazolones was synthesized, and their inhibitory effects against PL were
Discovery of pyrazolones as novel carboxylesterase 2 inhibitors that potently inhibit the adipogenesis in cells
Qian, Xing-Kai,Zhang, Jing,Song, Pei-Fang,Zhao, Yi-Su,Ma, Hong-Ying,Jin, Qiang,Wang, Dan-Dan,Guan, Xiao-Qing,Li, Shi-Yang,Bao, XiaoZe,Zou, Li-Wei
, (2021/05/10)
Carboxylesterase 2 (CES2) is one of the most important Phase I drug metabolizing enzymes in the carboxylesterase family. It plays crucial roles in the bioavailability of oral ester prodrugs and the therapeutic effect of some anticancer drugs such as irino
Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters
Tan, Fei,Pu, Maoping,He, Jun,Li, Jinzhao,Yang, Jian,Dong, Shunxi,Liu, Xiaohua,Wu, Yun-Dong,Feng, Xiaoming
supporting information, p. 2394 - 2402 (2021/02/16)
The homologation of ketones with diazo compounds is a useful strategy to synthesize one-carbon chain-extended acyclic ketones or ring-expanded cyclic ketones. However, the asymmetric homologation of acyclic ketones with α-diazo esters remains a challenge due to the lower reactivity and complicated selectivity. Herein, we report the enantioselective catalytic homologation of acetophenone and related derivatives with α-alkyl α-diazo esters utilizing a chiral scandium(III) N,N′-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under slightly modified conditions, affording a series of enantioenriched cyclic β-keto esters. Density functional theory calculations have been carried out to elucidate the reaction pathway and possible working models that can explain the observed regio- and enantioselectivity.
FeCl3·6H2O-catalyzed selective conjugate reduction of alkylidene-β-keto esters and alkylidene-1,3-diketones
Syamala, Lakshmi V.R. Babu,Mete, Trimbak B.,Bhat, Ramakrishna G.
, p. 3288 - 3291 (2018/07/25)
FeCl3·6H2O/triethylsilane composite catalyst system is successfully developed for the selective conjugate reduction of carbon-carbon double bond of Michael acceptor-alkylidene-β-keto esters and alkylidene-1,3-diketones under mild rea
Catalytic Enantioselective Protonation/Nucleophilic Addition of Diazoesters with Chiral Oxazaborolidinium Ion Activated Carboxylic Acids
Kang, Ki-Tae,Kim, Seung Tae,Hwang, Geum-Sook,Ryu, Do Hyun
supporting information, p. 3977 - 3981 (2017/03/27)
A new chiral Br?nsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids.
Redox-Annulation of Cyclic Amines and β-Ketoaldehydes
Chen, Weijie,Seidel, Daniel
supporting information, p. 1024 - 1027 (2016/03/15)
Benzo[a]quinolizine-2-one derivatives are readily assembled from 1,2,3,4-tetrahydroisoquinoline and β-ketoaldehydes by means of a new intramolecular redox-Mannich process. These reactions are promoted by simple acetic acid and are thought to involve azomethine ylides as reactive intermediates.
Catalytic asymmetric insertion of diazoesters into Aryl-CHO bonds: Highly enantioselective construction of chiral all-carbon quaternary centers
Gao, Lizhu,Kang, Byung Chul,Ryu, Do Hyun
supporting information, p. 14556 - 14559 (2013/10/22)
This paper describes a catalytic enantioselective route to synthesize functionalized all-carbon quaternary acyclic systems via a boron Lewis acid-promoted formal C-C insertion of diazoesters into aryl-CHO bonds. In the presence of chiral (S)-oxazaborolidinium cation 1d as a catalyst, the reaction proceeded in good yield (up to 83%) with good regioselectivity (up to 88:12) and excellent enantioselectivity (up to 99% ee). The synthetic potential of this method was illustrated by conversion of the products to both α-and β-amino esters.
H5CoW12O40 supported on nano silica from rice husk ash: A green bifunctional catalyst for the reaction of alcohols with cyclic and acyclic 1,3-dicarbonyl compounds
Rafiee, Ezzat,Khodayari, Maryam,Kahrizi, Masoud,Tayebee, Reza
experimental part, p. 121 - 128 (2012/06/01)
Rice husk ash (RHA) is an abundant agricultural by-product. The present research work deals with the production of nano silica powders, with high surface area and in amorphous form, from RHA using optimized technique. 12-Tungestocobaltic acid, H5CoW12O40 (CoW), was supported on silica from RHA to produce silica supported CoW (CoW/NSiO 2) as a nano catalyst. The characterization data derived from FT-IR reveal that the Keggin structure of CoW remains intact in CoW/NSiO2. TEM image showed that the catalyst had spherical shape with an average particle size of 10 nm. The acidity of the catalyst was measured by potentiometric titration with n-butylamine. To our surprise, this very strong solid acid catalyst showed an excellent distribution of acid sites, suggesting that the catalyst possesses a higher number of surface active sites compared to CoW supported on commercial silica (CoW/SiO2), CoW and K 5CoW12O40. A high catalytic activity was found over CoW/NSiO2. Finally, CoW/NSiO2 has been used as a highly effective catalyst for benzylation of linear 1,3-dicarbonyl compounds with benzylic alcohols and synthesis of β-keto enol ethers from cyclic 1,3-dicarbonyl compounds. The present methodology offers a practical, simple, mild, environmentally friendly, and timesaving method under solvent-free conditions.
Different products in the reaction of the alcohols with cyclic and acyclic 1,3-dicarbonyl compounds: K5CoW12O40 as an electron transfer nano catalyst
Rafiee, Ezzat,Kahrizi, Masoud,Joshaghani, Mohammad
, p. 1363 - 1366 (2013/02/22)
K5CoW12O40 was used as a highly effective catalyst for the benzylation of 1,3-dicarbonyl compounds. β-Keto enol ethers were obtained when cyclic 1,3-dicarbonyl compounds used in this conditions instead of linear ones. The present methodology offers a practical, simple, mild, environmentally friendly, and time-saving method for etherification. Very low loading of catalyst, ease of workup, ease of handling, and reusability of catalyst are other advantages of this catalyst.
